Dimethylformamide → HCID 68493393, compound

HRID 21244Notes

Reaction equation

HRID 21244 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[C:5]([NH:7][C:8]([CH3:16])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:9])=[O:6].CN(CCN(C)C)C.CN([CH:33]=[O:34])C>C1COCC1>[Cl:1][C:2]1[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[C:4]2[C:3]=1[CH:33]([OH:34])[N:7]([C:8]([CH3:16])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:9])[C:5]2=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 684891313-chloro-4-methoxy-N-(1-methyl-1-phenylethyl)benzamide

Product 1

HCID 68493393HCID 68493393, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Step 2 of Example 16, 3-chloro-4-methoxy-N-(1-methyl-1-phenylethyl)benzamide (500 mg, 1.65 mmol) was dissolved in THF (20 mL), and the solution was treated with TMEDA (0.80 mL, 5.3 mmol), sec-butyl lithium-hexane solution (0.99 mol/L, 5.3 mL, 5.3 mmol) and DMF (0.281 mL, 3.63 mmol), followed by purification by slurry using diisopropylether to obtain 4-chloro-5-methoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (385 mg, yield 71%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-84c838dc16f84dc1a257cb4dda6c43bc
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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